Which Harper’s Bazaar cover do you prefer? I like the one on the right. Gwyneth Paltrow’s hat and veil combined with the minimalistic design recall the bold fashion magazine covers of the 1960’s. Whereas the cover on the left has the star almost crowded out with busy, vague headlines like “Ten Looks For Now” and “Your Best Body Ever!” It looks like a Cosmopolitan cover.

But what do I know? The people at Harper’s Bazaar have more faith in the cover on the left–they’re sending it to the newsstands while loyal subscribers get the other one. Either way, Paltrow was a safe pick. The actor’s icy blue eyes have reliably sold magazines since the mid-1990’s.

When we look at her, we don’t just see a talented actor and pretty face. We see a red carpet staple, a writer of cookbooks, and a self-styled online lifestyle guru. We also see the wife of Chris Martin and the ex of Hollywood hunks Brad Pitt and Ben Affleck. Our entire prior knowledge of Paltrow, on and off the screen, flashes through our minds before we’ve finished reading the headlines.

What we don’t remember right away is Paltrow’s age. She’s 40.

Dick Stolley, founding managing editor of People magazine, once distilled the process of choosing a magazine cover subject into a list of matchups.

“Young is better than old. …Pretty is better than ugly. …Rich is better than poor. …Movies are better than music. …Music is better than television. …Television is better than sports …. . . and anything is better than politics.”

Later he added “…And nothing is better than the celebrity dead” after memorial covers of John Lennon and Princess Diana proved to be the magazine’s top sellers. But is Stolley’s mantra still correct? Is young really better than old?

This question swirled in my head after I read widely successful singer-songwriter Taylor Swift had difficulty moving magazines. Buzzfeed reports Swift was the worst selling cover model in the six-month period ending in June 2012. She bombed on Cosmopolitan, was disappointing for Glamour and Harper’s Bazaar, and tanked on the covers of Elle and Marie Claire in 2010. The 23-year old is arguably one of the most popular musicians of the moment with a large fan base who accept her heartbreak songs as their own. What gives?

Nineteen-year-old Justin Bieber has a similar problem with magazine covers. As WWD reports, “In 2011, he was Vanity Fair‘s worst seller and sold five percent below average for Rolling Stone. Last year, he was Rolling Stone‘s worst seller in the second half, according to the Alliance of Audited Media.” The occasion is his appearance on the cover of Teen Vogue‘s May issue. As Hilary Moss points out, the editors aren’t relying on his pretty face alone–the headline “Justin’s Crazy Year” refers to the star’s recent Twitter meltdowns, hospitalization, and abandoned pet monkey.

We live in a culture obsessed with youth. Advertisers chase allowance money and celebrities kill facial muscles with Botox. But what if youthful inexperience was actually a hindrance when it came to moving magazines?

“I don’t want to say it’s the fault of anyone at the magazine,” says PJ Tarasuk, who used to book the covers of Chatelaine, Fashion and its tween spinoff Fashion 18. “By putting Justin or Taylor on the cover they want to be relevant, because they’re definitely topical right now. But their audience doesn’t care about them. I don’t think they have enough meat in their lives to be a fully realized feature.” (Throughout our interview, Tarasuk uses the word “meat” to connote the type of juicy life stories that people want to read about.)

According to Tarasuk, young stars like Bieber and Swift do well in gossip magazines like People because People writes in sound bites. But with a magazine like Vanity Fair, readers expect intelligent, in-depth features. By putting Bieber on the cover, they alienate their core audience without gaining a younger one. Bieber’s Twitter army most likely scoped out the photos online.

The styling of the magazine cover is of the utmost importance. One of the few times Tarasuk was really shocked by how well an issue he worked on sold concerned a cover with Kristin Kreuk.

“When it was focus grouped we discovered it was because teenage boys had picked up the issue, thinking it was a Maxim or one of those magazines. So the audience that we wanted to pick it up, teenage girls or young women, picked up the issue fine, but the issue went gangbusters because of the fan boys who were interested in her because of Smallville.”

I asked if it was because the cover was sexy.

“It was a summer cover, so she was wearing… less than a winter cover. There were those Maxim covers that were ridiculous for a while, where the woman would only have her areolas covered, or she’d have her finger in her mouth suggesting… whatever! It certainly wasn’t suggestive that way at all.”

Fashion 18 tried to repeat the same success the next year with a different young starlet. Anna Paquin was in the new X-Men film, so the stylists glammed her up and dressed her in even less clothes than Kruek. “I think she had a hoodie and a small bikini top,” Tarasuk said. “Again, not sexually at all, but still summer clothing.” The issue sold respectfully, but they didn’t attract the fan boys they expected. “Maybe Anna Paquin wasn’t considered sexy at the time,” he admits. “It wasn’t until True Blood that she started to move covers off the shelf.”

Tarasuk argues that some of the most successful styling is when teen stars transition to being adult, citing a Selena Gomez cover he did which was the first time she looked grown up. “Now that Justin Bieber’s covers have moved him from teenage boy into manhood they do better,” he says.

Age and life experience are some of the reasons celebrities have replaced models as fashion magazine cover models. Back in the Supermodel heyday, Linda Evangelista and Naomi Campbell had life stories and personalities the reader cared about. “I don’t want to say that models became boring…” he begins, but points out that when a young woman is picked out at 15, flown to New York for the shows, and goes back to her “boyfriend from Pickton, Ontario,” it doesn’t exactly lead to compelling stories.

Now if only editors would recognize a face with a few wrinkles represents those interesting life stories, rather than something to be airbrushed into oblivion.

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Max Mosher writes about style for Toronto Standard. You can follow him on Twitter at @max_mosher_.